A Highly Selective, Polymer-Supported Organocatalyst for Michael Additions with Enzyme-Like Behavior

被引:99
作者
Alza, Esther [1 ]
Pericas, Miquel A. [1 ,2 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
关键词
asymmetric catalysis; Michael addition; nitroolefins; organocatalysis; synthetic enzymes; ENANTIOSELECTIVE MICHAEL; BETA-NITROSTYRENES; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; ASYMMETRIC ORGANOCATALYSTS; PYRROLIDINE SULFONAMIDE; 1,4-ADDITION REACTIONS; CONJUGATE ADDITION; CLICK CHEMISTRY; CHIRAL AMINES; SILYL ETHER;
D O I
10.1002/adsc.200900817
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A polymer-supported alpha,alpha-diarylprolinol silyl ether displays catalytic activity and enantioselectivity comparable to the best homogeneous catalysts in the Michael addition of aldehydes to nitro-olefins. Above all, the combination of polymer backbone, triazole linker, and catalytic unit confers to it an unprecedented substrate selectivity in favor of linear, short-chain aldehydes.
引用
收藏
页码:3051 / 3056
页数:6
相关论文
共 71 条
  • [1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
    Alexakis, A
    Andrey, O
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
  • [2] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [3] Highly enantioselective Michael additions in water catalyzed by a PS-Supported pyrrolidine
    Alza, Esther
    Cambeiro, Xacobe C.
    Jimeno, Ciril
    Pericas, Miquel A.
    [J]. ORGANIC LETTERS, 2007, 9 (19) : 3717 - 3720
  • [4] A Solid-Supported Organocatalyst for Highly Stereoselective, Batch, and Continuous-Flow Mannich Reactions
    Alza, Esther
    Rodriguez-Escrich, Carles
    Sayalero, Sonia
    Bastero, Amaia
    Pericas, Miquel A.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) : 10167 - 10172
  • [5] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins
    Andrey, O
    Alexakis, A
    Tomassini, A
    Bernardinelli, G
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168
  • [6] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [7] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
    Betancort, JM
    Barbas, CF
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
  • [8] Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins
    Cao, Chun-Li
    Ye, Meng-Chun
    Sun, Xiu-Li
    Tang, Yong
    [J]. ORGANIC LETTERS, 2006, 8 (14) : 2901 - 2904
  • [9] Pyrrolidine-Camphor Derivative as an Organocatalyst for Asymmetic Michael Additions of α,α-Disubstituted Aldehydes to β-Nitroalkenes: Construction of Quaternary Carbon-Bearing Aldehydes under Solvent-Free Conditions
    Chang, Chihliang
    Li, Ssu-Hsien
    Reddy, Raju Jannapu
    Chen, Kwunmin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (09) : 1273 - 1278
  • [10] Highly enantioselective Michael addition reactions in water catalyzed by an insoluble MPS-supported 4-sulfonamidyl prolinol tert-butyldiphenylsilyl ether
    Chuan, Yongming
    Chen, Guihua
    Peng, Yungui
    [J]. TETRAHEDRON LETTERS, 2009, 50 (25) : 3054 - 3058